CA2882658A1 - Coating composition with trisamine functionalized dispersant - Google Patents

Coating composition with trisamine functionalized dispersant Download PDF

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Publication number
CA2882658A1
CA2882658A1 CA2882658A CA2882658A CA2882658A1 CA 2882658 A1 CA2882658 A1 CA 2882658A1 CA 2882658 A CA2882658 A CA 2882658A CA 2882658 A CA2882658 A CA 2882658A CA 2882658 A1 CA2882658 A1 CA 2882658A1
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CA
Canada
Prior art keywords
composition
dispersant
tris
structural units
hydroxymethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA2882658A
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French (fr)
Inventor
Sudhakar Balijepalli
Lidaris San Miguel Rivera
Shubhangi Hemant Nair
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Dow Global Technologies LLC
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Dow Global Technologies LLC
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Filing date
Publication date
Application filed by Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Publication of CA2882658A1 publication Critical patent/CA2882658A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/43—Thickening agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09D201/025—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09D201/06—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
    • C09D201/08—Carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • C09D5/027—Dispersing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/45—Anti-settling agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2237—Oxides; Hydroxides of metals of titanium
    • C08K2003/2241—Titanium dioxide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • C08L101/14—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

The present invention relates to a composition comprising a stable aqueous dispersion of polymer particles and a dispersant adsorbed onto the surfaces of TiO2 particles, wherein the dispersant is a water-soluble polymer functionalized with structural units of a carboxylic acid ester and tris(hydroxymethyl)aminomethane. The composition of the present invention is particularly useful for achieving high hiding for paints containing associative thickeners.

Description

Coating Composition with Trisamine Functionalized Dispersant Background of the Invention The present invention relates to a coating composition containing a trisamine functionalized dispersant. The dispersant is useful in promoting hiding in a paint formulation.
Paints containing associative rheology modifiers such as hydrophobically modified ethylene oxide urethane (HEUR), hydrophobically modified alkali soluble emulsion (HASE), and hydrophobically modified hydroxylethyl cellulose (HMHEC) thickeners cause latex particles to self-associate, resulting in self-association (crowding) of TiO2 particles, thereby reducing hiding efficiency as compared to compositions thickened with non-associative thickeners.
This crowding effect occurs because associative rheology modifiers create a network with the binder in the paint system, thereby pushing TiO2 particles closer together. It would therefore be desirable to discover a way to improve the hiding efficiency of coatings formulated with associative rheology modifiers.
Summary of the Invention The present invention addresses a need in the art by providing a composition comprising a stable aqueous dispersion of polymer particles and a dispersant adsorbed onto the surfaces of TiO2 particles, wherein the dispersant is a water-soluble polymer functionalized with structural units of a carboxylic acid ester monomer and tris(hydroxymethyl)aminomethane.
The present invention addresses a need in the art by providing a way of improving hiding in a paint formulation thickened with an associative thickener.
Detailed Description of the Invention The present invention addresses a need in the art by providing a composition comprising a stable aqueous dispersion of polymer particles and a dispersant adsorbed onto the surfaces of TiO2 particles, wherein the dispersant is a water-soluble polymer functionalized with structural units of a carboxylic acid ester monomer and tris(hydroxymethyl)aminomethane.

A structural unit of a carboxylic acid ester monomer is illustrated:

where R is H or methyl, RI is a C1-C20 alkyl group, and the dashed lines represent the points of attachment of the unit to the polymer backbone.
A structural unit of tris(hydroxymethyl)methane is represented by a transamidation unit or a transesterification unit or both:

XOH or OOH
õs OH
HO
õs Transamidation unit Transesterification unit The dispersant can be prepared by contacting tris(hydroxymethyl)amine with a polymer functionalized with structural units of a carboxylic acid ester monomer, preferably a homopolymer of methyl methacrylate, in the presence of a suitable catalyst such as dibutyl tin oxide in the presence of a high boiling solvent such as N-methylpyrrolidone at an advanced temperature, preferably in the range of 150 C to 200 C. The dispersant can also be prepared by copolymerizing tris(hydroxymethyl)acrylamide with a carboxylic acid ester monomer such as methyl methacrylate.
The resulting polymer preferably contains both transamidation and transesterification units, preferably at a mole:mole ratio of 2:1 to 10:1 in favor of transamidation; the polymer also preferably contains structural units of unreacted carboxylic acid ester, preferably methyl methacrylate.
Preferably, the mol-to-mol ratio of structural units of tris(hydroxymethyl)methane to structural units of the carboxylic acid ester monomer, preferably methyl methacrylate, is in
2 =

the range of 40:60 to 90:10. A preferred M for the dispersant is in the range of 1000 to 25,000 g/mol.
The composition of the present invention can be prepared by contacting together the dispersant, the stable aqueous dispersion of polymer particles, and the Ti02.
The composition may further include one or more of the following materials:
rheology modifiers;
opaque polymers; fillers; colorants, other pigments including encapsulated or partially encapsulated pigments and opaque pigments; dispersants; wetting aids;
dispersing aids;
dispersant adjuvants; surfactants; co-solvents; coalescing agents and plasticizers; defoamers;
preservatives; anti-mar additives; flow agents; leveling agents; slip additives; and neutralizing agents.
In the following examples, polymethylmethacrylate was obtained from Aldrich and was reported to have an M, of ¨15,000 g/mol (Example 1) and ¨5300 g/mol (Example 2).
Examples Example 1 ¨ Preparation of Poly(methyl methacrylate)-g-Tris(hydroxymethyl)aminomethane Polymethylmethacrylate (20 g, M = 15,000 g/mol as supplied by Aldrich), tris(hydroxymethyl)aminomethane (70 g), N-methyl-2-pyrrolidone (NMP, 40 mL) and dibutyl tin oxide (500 mg) were mixed and heated to 190 ¨200 C in a reaction flask equipped with a reflux condenser for 2 h. The product was cooled and precipitated in diethyl ether, then dried at in vacuo 60 C. This polymer was reprecipitated by dissolution in NMP
and precipitating in diethyl ether, then re-dried at 60 C in vacuo.
Example 2 ¨ Preparation of Poly(methyl methacrylate)-g-Tris(hydroxymethyl)aminomethane The procedure from example 1 was followed substantially as described except that a polymethylmethacrylate having a M of 5,300 g/mol was used.
Paint Formulation Paint formulations were prepared using Examples 1 and 2 as well as a comparative formulation using TAMOLTm 2002 Dispersant (a hydrophobic polyacid copolymer).
In the following Table 1, TiO2 refers to Ti-Pure R-706 Ti02, SG-10M refers to RHOPLEXTM SG-10M Acrylic Copolymer, Texanol refers to Texanol Coalescent, RM-refers to ACRYSOLTM RM-2020 NPR Rheology Modifier, RM-825 refers to ACRYSOLTM
3 RM-825 Rheology Modifier, and 15-S-9 refers to TERGITOLTm 15-S-9 Surfactant.
(TAMPOLTm, RHOPLEXTM, ACRYSOLTM, and TERGITOLTm are all Trademarks of The Dow Chemical Company or its Affiliates.) Table 1 ¨ Paint formulation Using Example 1 or Example 2 Dispersant Grind Weight (g) Dispersant (dry) 0.07 Water 1.68 TiO2 4.69 Grind Sub-Total 6.44 Letdown SG-10M 13.94 Texanol 0.56 Water 3.55 RM-2020 0.56 RM-825 0.015 15-S-9 0.1 Letdown sub-total 18.72 Total 25.16 The paints were coated on a Leneta chart and Hiding (S/mil) was determined using the Kubelka-Munk S/mil Test Method.
Kubelka-Munk S/mil Test Method:
Two draw-downs were prepared on Black Release Charts (Leneta Form RC-BC) for each paint using a 1.5-mil Bird draw down bar and the charts allowed to dry overnight. Using a template, 3.25"x 4" rectangles were cut out with an X-ACTO knife on each chart. The Y-reflectance was measured using a BYK Gardner Spectro-guide 45/0 Gloss Color spectrophotometer in each of the scribed areas five times measuring on a diagonal starting at the top of the rectangle and the average Y-reflectance recorded. A thick film draw down was prepared for each paint on Black Vinyl Charts (Leneta Form P121-10N) using a 3" 25 mil block draw down bar and the charts were allowed to dry overnight. The Y-reflectance was
4 ' measured in five different areas of the draw down and the average Y-reflectance recorded.
Kubelka-Munk hiding value S is given by Equation 1:
Equation 1 R
x1n1 ¨ (R B x R) S =
X x (1¨ R2) R

R
where X is the average film thickness, R is the average reflectance of the thick film and RB is the average reflectance over black of the thin film. X can be calculated from the weight of the paint film (Wpf), the density (D) of the dry film; and the film area (A).
Film area for a 3.25" x 4" template was 13 in2.
W pf (g) x 1000(mii / in) X(mils) = ___________________________________ D(lbs I gal) x 1.964(g / in' I lbs I gal)x A(in ) The hiding values for the formulated paints are shown in Table 2.
Example No. Dispersant in Paint Formulation 5/mil Example 1 PMMA-Tris Mw = 15 K 6.54 Example 2 PMMA-Tris Mw = 5.2 K 6.52 Comparative 1 TAMOL 2002 Dispersant 5.64 The results demonstrate that excellent hiding can be achieved in paint formulations containing an associative thickener (in these examples, a HEUR thickener) using the PMMA-Tris dispersants of the present invention.
5

Claims (5)

Claims
1. A composition comprising a stable aqueous dispersion of polymer particles and a dispersant adsorbed onto the surfaces of TiO2 particles, wherein the dispersant is a water-soluble polymer functionalized with structural units of a carboxylic acid ester and tris(hydroxymethyl)aminomethane.
2. The composition of Claim 1 wherein the carboxylic acid ester is methyl methacrylate.
3. The composition of Claim 2 wherein the mol-to-mol ratio of structural units of tris(hydroxymethyl)aminomethane to structural units of methyl methacrylate is in the range of 40:60 to 90:10.
4. The composition of any of Claims 1 to 3 which further includes an associative thickener.
5. The composition of any of Claims 1 to 3 which further includes one or more materials selected from the group consisting of rheology modifiers; opaque polymers;
fillers; colorants, other pigments including encapsulated or partially encapsulated pigments and opaque pigments; dispersants; wetting aids; dispersing aids; dispersant adjuvants;
surfactants; co-solvents; coalescing agents and plasticizers; defoamers; preservatives; anti-mar additives;
flow agents; leveling agents; slip additives; and neutralizing agents.
CA2882658A 2014-03-07 2015-02-23 Coating composition with trisamine functionalized dispersant Abandoned CA2882658A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201461949471P 2014-03-07 2014-03-07
US61/949,471 2014-03-07

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CA2882658A1 true CA2882658A1 (en) 2015-09-07

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EP (1) EP2915855B1 (en)
CN (1) CN104893399A (en)
AU (1) AU2015200911A1 (en)
BR (1) BR102015003699A2 (en)
CA (1) CA2882658A1 (en)
MX (1) MX344164B (en)

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US11206895B2 (en) * 2016-04-21 2021-12-28 Nike, Inc. Sole structure with customizable bladder network
EP3523381B1 (en) 2016-10-07 2020-12-09 Basf Se Latex paint containing titanium dioxide pigment
WO2018065574A1 (en) 2016-10-07 2018-04-12 Basf Se Latex paint containing titanium dioxide pigment

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DE3208791A1 (en) * 1982-03-11 1983-09-22 Röhm GmbH, 6100 Darmstadt METHOD FOR COATING MEDICINAL PRODUCTS BY MEANS OF A COATING AGENT DISPERSED IN WATER
US4731419A (en) 1986-02-24 1988-03-15 Nalco Chemical Company Alkoxylated/cationically modified amide-containing polymers
WO1993012184A1 (en) * 1991-12-03 1993-06-24 Rohm And Haas Company Process for particle adsorption
FR2816610B1 (en) * 2000-11-10 2003-08-15 Rhodia Chimie Sa AQUEOUS TITANIUM DIOXIDE DISPERSION, SUBSTRATE OBTAINED THEREFROM AND SELF-CLEANING METHOD OF SAID SUBSTRATE
US20050282946A1 (en) * 2004-06-21 2005-12-22 Tyau-Jeen Lin Titanium dioxide slurries for ink applications
US20090269510A1 (en) * 2008-04-25 2009-10-29 Daniel Lieberman Printed electronics by metal plating through uv light
EP2161304B1 (en) 2008-09-04 2014-04-23 Rohm and Haas Company Opacifying pigment particle
JP2010163580A (en) * 2009-01-19 2010-07-29 Fujifilm Corp Method for producing pigment dispersion, pigment dispersion, and ink for inkjet recording
JP2010174152A (en) * 2009-01-30 2010-08-12 Fujifilm Corp Method for manufacturing pigment dispersion liquid, pigment dispersion liquid, ink for ink jet recording, and image recording method
JP5689455B2 (en) * 2009-03-16 2015-03-25 ダウ グローバル テクノロジーズ エルエルシー Dispersion and process for producing the dispersion
EP2253676A1 (en) * 2009-05-19 2010-11-24 Rohm and Haas Company Opacifying pigment particle
MX2013014688A (en) * 2011-06-30 2014-02-20 Rohm & Haas Composition containing associative rheology modifier and polymer encapsulated pigment particles.
CA2818445C (en) * 2012-07-31 2020-07-14 Rohm And Haas Company Sulfonic acid monomer based compositions
CA2818446C (en) * 2012-07-31 2021-03-02 Rohm And Haas Company Sulfonic acid monomer based compositions

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CN104893399A (en) 2015-09-09
MX2015002311A (en) 2015-09-07
US20150252213A1 (en) 2015-09-10
US9150752B2 (en) 2015-10-06
BR102015003699A2 (en) 2017-05-02
EP2915855A1 (en) 2015-09-09
MX344164B (en) 2016-12-07
EP2915855B1 (en) 2016-04-27
AU2015200911A1 (en) 2015-09-24

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Effective date: 20190225